Jake Gyllenhaal Movies

Eight Awesome Movies Jake Gyllenhaal Made Before 'Southpaw'

Right now, Jake Gyllenhaal is killing it. There is nobody better. We will wait while you stop scoffing and then we will ask you to, if you disagree, suggest an actor who has had a better run of late. Chris Pratt? Great, but he’s only three films in. Ryan Gosling? His last knock out role was in 2011. Michael Fassbender? We will hear your argument but we will still win. In the past 15 years, and especially the last three, Jake Gyllenhaal has amassed a collection of roles to match anything anyone else has done in the same time. He’s going for it again in boxing movie Southpaw. Join us as we journey through his path to unmatched excellence.

Donnie Darko

Pandora Cinema

Pointing out that Donnie Darko is great is similar to saying, “Hey did you see that Citizen Kane? Good movie,” but it is included here as illustration of the great choices Gyllenhaal has made since his early days. (You can go back further, if you like, but Donnie Darko is when he became interesting. City Slickers is not a classic.) This film sowed a seed for a love of the uncategorisable that’s become more pronounced in the last few years.

The Good Girl

Fox Searchlight Pictures

The first rom-com you do as a rising star is supposed to be something fluffy where you wind up kissing somewhere in New York, back-lit by fairy lights. Instead, Gyllenhaal made this indie in which he plays a teenager who starts a doomed affair with a married woman who works in the same supermarket (Jennifer Aniston, in the best role of her movie career – yes, we’ve seen Cake). There’s an edge to Gyllenhaal’s character that always seems a little off, like he might snap at any second. Let us not speak of his later, totally standard rom-com Love and Other Drugs, which we’ll assume he made due to a large tax bill.

Brokeback Mountain

Focus Features

Let’s put aside for a second that most ‘name’ actors wouldn’t touch this film because it was ‘the gay cowboy movie’. (Side note: can you imagine that even being an issue now, just ten years on? Things have changed a lot, but then it was a big deal and taking the film was brave.) Heath Ledger got a great deal of the attention for playing the more repressed of the two characters, but nothing should be taken away from Gyllenhaal, who – as the character who wanted to accept being gay and try to live a life – had to show just as much pain, but in a more raw way.

Jarhead

Universal Pictures

Considered by many to be a failure in Sam Mendes’s directing career, but in the sense that it achieves its aims, it’s a success. It was judged as a war movie and if you treat it as that then it’s a bit lacking in actual warfare. But it’s not a war movie, it’s an absence of war movie, about how soldiers have become almost outmoded in modern warfare. Gyllenhaal plays a sniper who, after dreaming of becoming a soldier and fighting for his country, spends his days always waiting and never seeing a moment of battle. The lack of action means it’s up to Gyllenhaal to propel the movie forward with, by definition, very little to act against. He nails the quality of an animal caged.

End of Watch

Open Road Films

By this point, Gyllenhaal could reasonably be just choosing big money paydays, which he did once with Prince of Persia and it was terrible, but instead he’s shown a propensity for smaller films by less experienced directors. Before directing End of Watch, David Ayer had written Training Day and Fast and Furious, and directed middle-level dramas Harsh Times and Street Kings, but he was not a big name. Ayer, Gyllenhaal and Michael Pena made this cop drama at its most arresting when simply sitting in the car with the two leads.

Prisoners

Warner Bros. Pictures

This. This is the moment Gyllenhaal comes into his own. There comes in some actors’ careers a director who just gets them, which is what Gyllenhaal found with Denis Villeneuve. Villeneuve turned what might have been a very standard kidnap thriller into a film about the way unsolved secrets can rip people apart. Gyllenhaal is the one person in the film just about holding things together, as the detective investigating the disappearance of two young girls. He has to absorb all the madness happening around him. It’s the quietest role in a film where all the other characters get a moment of explosior – and as such, the hardest.

Enemy

A24 Films

Villeneuve pushed Gyllenhaal even further in their second film together. It doesn’t matter if you like the film – and Denis Villeneuve makes no effort to coddle you – Gyllenhaal is mesmerising. He plays a teacher who one day watches a film and notices that one of the actors in it looks exactly like him. He tracks down this doppelganger and tries to work out why they are identical. Are they related? Are they the same person? The switch between playing both men is so delicate that most actors would get lost in it, or give in to the temptation to give the two men some identifying tick. It’s the sort of film that has so much potential to be disastrous – the end is willfully insane – yet, in no small part due to Gyllenhaal, it’s like the kind of dream that obsesses you for weeks and that you bore your friends with.

Nightcrawler

Open Road Films

There is not one person on the list of Best Actor Oscar nominees in 2015 that you could reasonably say did a better job than Gyllenhaal in this movie, including Eddie Redmayne, who won. Bradley Cooper? Please. Gyllenhaal as the hollow-eyed, ruthless Louis Bloom was the performance of 2014, hands down. He haunts that movie. It’s more of a transformation movie than Southpaw, with just enough weight lost that his eyes sink and throw all his proportions off. He makes Louis, a man who wants to muscle into the grubby world of video crime journalism, a wholly unnatural person. Not in the sense of being unbelievable, but in the sense that none of his actions seem to come from a place of normal human emotion. Show us someone who’s better. Go on. Whoever you are currently pointing at, you are WRONG.